Sodium triacetoxyborohydride → benzyl 2,4-bis(benzyloxy)-6-(2-(dimethylamino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-5-methylnicotinate

HRID 1481798ノート

反応式

HRID 1481798 の反応式
[CH2:1]([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:33]=[CH:32][C:31]3[N:30]4[CH2:34][CH:35]([NH:37][CH3:38])[CH2:36][C:29]4=[CH:28][C:27]=3[CH:26]=2)[C:22]([CH3:39])=[C:21]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:48](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C=O>[CH2:1]([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:33]=[CH:32][C:31]3[N:30]4[CH2:34][CH:35]([N:37]([CH3:48])[CH3:38])[CH2:36][C:29]4=[CH:28][C:27]=3[CH:26]=2)[C:22]([CH3:39])=[C:21]([O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 5049666Sodium triacetoxyborohydrideHCID 71284780benzyl 2,4-bis(benzyloxy)-5-methyl-6-(2-(methylamino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)nicotinate

生成物 1

HCID 71285017benzyl 2,4-bis(benzyloxy)-6-(2-(dimethylamino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-5-methylnicotinate収率 78.4%

試薬・触媒・溶媒 2

HCID 712Formaldehyde触媒HCID 111,2-Dichloroethane溶媒

実験手順

The product from Example 415, Step 2 (31 mg, 0.05 mmol) was dissolved in 1,2-dichloroethane (1 mL). Aqueous 30% formaldehyde (1 drop, ˜0.2 mmol) was added to the mixture, followed by sodium triacetoxyborohydride (21 mg, 0.1 mmol). The mixture stirred at room temperature for 30 min. The mixture was loaded directly to silica gel, eluting with 0-8% MeOH in CH2Cl2 to afford product (25 mg, 78%). LC-MS 638.3 [M+H]+, RT 1.21 min.

後処理

  1. washeluting with 0-8% MeOH in CH2Cl2

出典と根拠

ORDレコード
ord-c48e144b44054a00aec8f38fbe6bb46a
出典データセット
uspto-grants-2016_08
特許番号
US09409905B2

反応ノート

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